Blair's Apprentice
by puzzlepirateking
Summary: What if Blair had recognized Jenny's potential and took her on as an apprentice.
1. Chapter 1

So I recently got into Gossip Girl, and after seeing what happens to Jenny later on, I am determined to give her a story that gives her an more successful and happy journey.

I own nothing

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><p>"Well, I guess there is a first for everything. Oh, and I'm keeping the jacket, if that's okay with you. Monday? Lunch on the Steps?" Jenny said to a shocked Blair as the younger girl made her way back towards that elevator that had brought her up.<p>

It took Blair a second to recover her wits before she replied with, "You are more than welcome to keep the jacket, call it a reward for getting away it, but you and me are going to be having a one on one lunch Monday, away from the rest of the minions."

Jenny gave Blair a suspicious look, before saying, "Okay, I'll play another game, see you on Monday."

**Gossip Girl: Word is Jenny Humphrey killed at Blair Waldorf's sleepover. It was a debut the like of which haven't been seen since Blair herself. In even bigger news, Jenny has earned herself a one on one lunch with Queen B on Monday, at the Queens request.**

/\/\/\/\/\/\/

Lunch on Monday finally came around, having taken what feels like forever for Jenny. She stood at the meeting spot waiting for Blair to appear. When she finally did, Jenny immediately notices a small stack of papers in her hand.

"Ah, good, you're here," Blair said, handing the papers to Jenny. "You and me are taking the rest of the day off, it's already been cleared with the administration, and there is notes and homework for the rest of your day. We have much to discuss."

Jenny just nodded and followed behind Blair as she headed out of the school and into one of Blair's limo. Soon enough the pair arrived back at Blair's house. Blair got out first, Jenny following close behind.

Once the pair gets up to the second floor, Blair held out a chair for Jenny to sit in. "Please, sit Jenny, as I said, we have a lot to discuss."

Jenny followed the instruction, taking a seat. Blair then moved to the seat across form her. "So, I'm just going to start with, you've impressed me. Not only did you pass the test, getting away with the jacket and not getting in trouble. I've posed that challenge to every other girl you saw at that party, and you are the only one who managed to do it, so bravo there. Then, on top of that, you defy me and leave the party. That is a bold move, and you have to be extremely confident to pull something like that off," Blair lays out.

"Okay, so what's this, a punishment?" Jenny asks nervously.

"Oh, absolutely not, quite the opposite in fact. I want you to become my apprentice, the next in line for the queen position. None of the girls have what it takes to become queen, but you, you on the other hand have the chops like nobody's business. I want to cultivate that," Blair explained to Jenny.

"Um…. Wow, I really don't know how to respond to that. I would love to do that, but are you sure it's alright. I can't do most of what the other girls can do, simply because I don't have the money to do it," Jenny told Blair.

"First off, don't be too hasty in taking this. I haven't explained what all it will entail. I will push you, and push you hard, in every aspect of your life, every idea in your head I will challenge, I expect you to fight, to become strong, to gain some thick skin, cause you will need it if you are going to survive in the outside world. I won't sugar coat this, I will be brutal on you. Do you still want to do this, even with that in the playing field?" Blair responds.

Jenny thought about it for a minute before responding with, "Absolutely."

Blair smiled, happy with the younger girl's decision. "Fantastic, I was really hoping that you would say that. If you hadn't, I would have had to find another person to succeed me, and the playing field is looking very bad if you aren't there. Now, onto the money issue. I'm planning on helping you a bit at the start, and teach you how to invest and make your own money, and then from there, you'll have to support yourself for the most part. You will need to work hard if you want this to work."

"Okay, how is this going to work?" Jenny said.

"Well, for starters, I was thinking of giving you a good million, and from there I'll work with you to find a small business to turn around and start making a profit with. On top of that, I'll teach you how to make your money do magic," Blair explained.

Jenny just stared at Blair for a couple seconds, trying to fathom that amount of money that Blair was going to put on her as a down payment. "Let me get this straight, you are going to put a million dollars into me off of me defying you at the slumber party," Jenny finally sputtered out.

"You don't give yourself enough credit Jenny, you did much more than just defying me that night, you made a statement, you got people talking, and you did something big just in defying me. You have guts too, something that none of the girls who grew up in money have. You have it because you've had to use them to get what you want before, instead of money, like the other bitches have. Yes, you are worth it, because you have all the parts to become one of the greatest queens of Constance," Blair explained to her new apprentice.

"Okay, only if you really think I'm worth it," Jenny said.

"First lesson dear Princess Jenny, you are always worth it. You may have insecurities about yourself, but let me be the only one that can see then, not the rest of the world. I am here to push you, but also to help you, to be your confidant. Know, no matter what I do to you, I respect and care for you," Blair said.

"Okay, can you start by trying to be nice to my brother?" Jenny asked.

"I figured that would come eventually, and I'm more than willing to do that. Now, let's get down to some of the gritty details," Blair said.

**Gossip Girl: Looks like little Jenny is no longer a small player in the game. I guess I'm the one to announce it to the world that it is now Princess Jenny, and you should bow down to her or face Queen B wrath.**

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><p>So, there it is, tell me what you think.<p> 


	2. Chapter 2

Whoops, accidentally posted the wrong Chapter 2, here's the right one.

I own nothing

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><p>Jenny ended up arriving home rather late that night, having been working through a fair amount of details with Blair about various different bits of business that were looking like they were going to pay off one day, such as setting up her new bank account.<p>

"You're getting in late," Rufus said, making his presence known to Jenny.

"I had a meeting with Blair, and I have to say it went well," Jenny replied.

"Ah, so Princess Jenny has decided to grace us with her presence," Dan said as he came out of his room.

"Princess Jenny, what's that about?" Rufus asked.

"Blair Waldorf, Queen B, made me an offer, to be her apprentice. I took her up on it," Jenny said.

"Really, you made a deal with Blair. She's manipulative and backstabbing, and it will not end well," Dan said.

"I am her apprentice now. I know that she will backstab and manipulate me, but in the end, she it will only be to make me a stronger person. It was part of her spiel that she did before she even allowed me to say yes," Jenny provided.

"So, you are basically Blair's top minion now?" Dan asked worriedly.

"I am more than that at this point. I am her student, she is going to be teaching me all that I need to know so I will succeed her when she leaves. She is investing a lot into me," Jenny replied.

"Really, what is she investing into you, her time, her torture, what?" Dan asked, starting to get annoyed with his sister.

"Considering that she is not only teaching me how to be Queen of the school, but also business, and is going to help me start up a business by the end of the year, I would be a little more lenient to her," Jenny told her family.

"What does she mean when she says help you start a business?" Rufus asked.

"It means that earlier today, she set up and gave me the keys to a bank account with a million of her money to buy and help run a business that should hopefully start turning a profit before the million is out," Jenny explained.

"Wait, Blair just gave you a million?" Dan asked.

"Yes, she did, I know, it's surprising, but it's true. She is actually going to be coming over tomorrow with some information about some different business types that we talked about today, and places here in Brooklyn that could sustain it. I have to do some research too into this stuff, and we are going to cross check our notes. I have homework to do, so I'll talk to you guys later," Jenny said before heading to her room.

The two boys stared left in the room stared at each other for a couple seconds before Rufus spoke, "I will need to talk to certain people quickly, but I think you should talk to Serena, it may clear things up in your mind."

Dan nodded and went into his own room. With a sigh, Rufus picked up the phone, dialing a number he didn't think he would have to anytime soon.

"Hello," the voice on the other end said.

"Hello Lily, I need some advice," Rufus said.

"Really, and you called me for it?" Lily asked.

"Well, I need some help dealing with my daughter who just became the apprentice to Blair Waldorf," Rufus replied.

"I can now see why you called me," Lily said.

/\/\/\/\/

"Hey Serena," Dan said into his phone as he was lying on his bed.

"Hey Dan, what's up?" Serena replied.

"Did you see the news about my sister?" Dan asked.

"I saw the slightly cryptic Gossip Girl post about it, and from it I'm guessing your sister did something big," Serena said.

"Well, she made a deal with Blair, and now she's Blair's apprentice," Dan told Serena.

"Wow, that's an honor," Serena said.

"What do you mean?" Dan asked.

"Being the apprentice of the current Constance queen is the highest honor in the school, beyond any of the accolades the school can give out. She is now the second most powerful girl in the entire school, on par with some of the staff to be honest. It also means that as soon as Blair leaves, Jenny will take her place. Her official title will be Princess Jenny. While the Gossip Girl post pointed towards it, I didn't think Blair would have the balls to actually take Jenny as her apprentice, as, no offense to you, but she is from Brooklyn," Serena explained to Dan.

"Okay, that doesn't alleviate much of my worries about this situation," Dan said.

"Okay, knowing Blair, she will push and prod every idea that Jenny has, but it is all with the purpose of both making Jenny as strong a person as possible, but also making it so she truly knows who she is, because that is just as important to being a good queen as having all the right skills," Serena said. "It will be hard on her, but it will be worth it, but expect Blair to become a good friend to her, if not more."

"More?" Dan asked.

"There have been some Queen/Princess pairs have become very close, even intimate. One of the big, unspoken rules of Constance, if this happens, no one comments on it, unless you want to never see New York again," Serena said.

"Okay, that would be something. Do I have to worry about this with Blair?" Dan asked.

"Yeah, you do. Blair is bi, having had a relationship with the previous Queen of Constance before she went off to college," Serena responded with.

"Wow, okay, yeah, I'll have to prepare myself for that I guess. I mean, I guess I have to prepare myself for any relationship that Jenny could go into, but with Blair, really," Dan said.

"It may or may not happen, it depends on how things work out with them, but it's completely possible," Serena replied.

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><p>Tell me what you think.<p> 


	3. Chapter 3

Hey guys, sorry this chapter took so long. College has been kicking my butt, so I've had basically no time, but thankfully the quarter is coming to a close so i should have a little more time to write soon, hopefully.

So here it is.

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><p>Blair arrived early the following day for school, know she would have to deal with her minions. She found that most of them were already there, and giving her some dirty looks. "I imagine that everyone has heard the news and I'm just guessing, but you aren't happy?" Blair said to her minions.<p>

"You expected anything else when you picked a girl for Brooklyn to be the next queen," Is said, speaking for the group.

"I knew this would be coming, but I remind you, one of the greatest queens to ever grace Constance, Queen Heather, was also from Brooklyn. Also, may it be said, she has guts, something that a queen needs, but none of you seem to have at all," Blair explained to her group of minions.

There was a couple seconds of silence as half the groups of minions were looking down in shame as the other half was still looking as smug as when Blair first arrived. "If you don't want to accept that you'll be following Jenny after I'm gone, then I can just boot you now and not cause Jenny the trouble when it comes her turn on the throne," Blair told the group, giving them an ultimatum.

The attitudes of all the minions quickly changed, as they realized just how serious Blair was about this. They all quickly nodded in compliance.

It was a few minutes later that Jenny arrived at the school, her presence and new position causing a little bit of a stir. She was soon standing right beside Blair, "Queen B."

"Princess J, lunch is on the steps today, you'll be right beside me," Blair informed Jenny before the first bell rang, signaling that it was almost time for class to start.

"I will see you there, Queen B," Jenny said heading off to her class.

Lunch ended up going smoothly, with none of the scathing comments pointed towards her that Jenny expected, though there was definitely a sense of grudging acceptance that Jenny sensed from the other girls. She continued to get that sense as she continued through the day, until the day ended and Jenny, for the second day in a row, got into Blair's limo, though this time she was heading home.

It took them only a handful of minutes to get back home, ending up easily beating Dan back. "Well, here we are. It's not much, but it's what we got," Jenny said hesitantly as she got out of the limo, Blair right behind her.

"So far it isn't too bad. It at least looks like it may be clean enough that I won't need to get a tetanus shot," Blair said in her normal sarcastic tone that made Jenny smile a little as she made her way up to her front door.

"Well, Queen Blair, welcome to my home," Jenny said as she swings the door open.

Blair walked in, assessing the place as she did. "Ah, you must be Blair Waldorf that Jenny cannot shut up about," Rufus said, making his presence known. Blair looked to where the voice came from, finding Rufus standing in the kitchen area.

"Ah, yes, that would be me. I'm guessing you would be Rufus, the dad," Blair said, making her way over to him, stopping on the other side of the breakfast bar.

"Yes, well, how long do you expect to be here? I can always make a little more if you'll be here for dinner," Rufus said.

"Well, I have no idea how long this will take, as we have to take care of a lot of business, though you will have your very own business owner by the end of the day, if everything goes well," Blair said.

"Well, you've met my dad, shall we head into my room now," Jenny said, grabbing Blair's attention.

"Yes, I would like to see my Princess's domain," Blair commented, following Jenny into her room.

"Well, here it is," Jenny said nervously.

Blair stepped in and took a couple seconds to look around, getting a grasp for the room. Her eyes settled on Jenny's sewing equipment. "I've never mentioned it before now, but you do some marvelous sewing. I remember seeing you at the Kiss On The Lips party and having to do a double take on how you had gotten a custom before realizing you had made it yourself," Blair commented.

Jenny blushed at Blair's words, "Thank you."

"You're welcome, now, let's get down to work. I have got a handful of prime locations for a starting up a clothing shop, though I think you could do some interesting line of your own within it," Blair told Jenny, as she pulled a stack of papers out of her school bag. Blair quickly separated them out and spread them across the bed.

"Okay, so out of the things we talked about yesterday, you think that clothing shop would be best?" Jenny asked

"I think it would work best for you. You have a talent for sewing, so you can make clothes that would only appear in your shop. Exclusivity is a draw, no matter what medium it comes from. Also, you will know what you are talking about with the clothes from the start instead of having to learn the more specific lingo of the trade," Blair explained to Jenny.

Jenny just nodded in response. "Okay, there are a good, three locations, that would work well for you to set up in. All of them are in walking distance of this loft. Now, each of them have advantages and disadvantages that we'll go through. I will be here to advise you, but I will not make the decision for you," Blair explained.

"Okay, let's get started," Jenny said.

Blair nodded before grabbing the first stack of papers, "Okay, first one is a small clothing shop that is struggling enough that they are looking for another person to come in and help. Now, it would be the cheapest of the options, being that the place is already mostly set up. There would be a couple changes, as I think the overall problem of the place is that it have a competing demographic with a larger franchise shop a couple stores down. Now, with you won't be able to be sole owner, which might be easier legally, but also means you will have to continually compromise and may not feel like the place is entirely be yours."

"Okay, I don't quite like the idea of sharing, but I won't count it out either," Jenny replied with.

Blair grabbed the next stack of papers, "Okay, next up is an abandoned building off in the bowels of Brooklyn. Now, this would be easy to procure, but also you would be tailoring the store strictly to Brooklyn."

"Maybe, what's the last one," Jenny replies.

Blair picks up the last stack of papers, "The last one is a currently open storefront on the edge of Brooklyn, closest to the Upper East Side. It will allow you to tailor the store to both Brooklyn and the Upper East Side. The issue is that this would be the biggest gamble out of all of them. Unlike the other two, you probably won't have enough money to start up something else if this fails."

"That one, definitely that one," Jenny replies.

"Okay, I will get it all set up for you, and then we will work on setting it up," Blair said, gathering up the various papers she had. "Now, I will go take care of that, start looking through your collection and determining what might work well on the rack. I will talk with you tomorrow," Blair instructed before leaving the room.

Blair closes the door behind her before heading up to Rufus. "I will be requiring Jenny tomorrow after school, but she doesn't know that yet, and you need to keep quiet about it," Blair tells her young charge's father.

"As her father I am required to inquire into the reasons," Rufus said.

"She will be meeting all the living former queens. She will find out on her way there, but we don't tell them ahead of time so they don't stress themselves out about it, as it's not a test, more of an introduction," Blair explained.

"Okay, well, just make sure she get home safe and has time to do her homework," Rufus said.

Blair nods in agreement before leaving the Humphrey loft.

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><p>Okay, there it is, tell me what you think.<p> 


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